US9642367B2 - Microbicidal composition - Google Patents

Microbicidal composition Download PDF

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Publication number
US9642367B2
US9642367B2 US15/108,485 US201415108485A US9642367B2 US 9642367 B2 US9642367 B2 US 9642367B2 US 201415108485 A US201415108485 A US 201415108485A US 9642367 B2 US9642367 B2 US 9642367B2
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acid
mbit
methyl
benzisothiazolin
growth
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US20160316756A1 (en
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Emerentiana Sianawati
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Dow Chemical Co
Nutrition and Biosciences USA 1 LLC
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Dow Global Technologies LLC
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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A01N37/04Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02Local antiseptics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10General cosmetic use
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/524Preservatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/23Solid substances, e.g. granules, powders, blocks, tablets
    • A61L2/232Solid substances, e.g. granules, powders, blocks, tablets layered or coated

Definitions

  • This invention relates to a synergistic combination of a selected microbicides having greater activity than would be observed for the individual microbicide.
  • MBIT is a new biocide chemistry which effectively preserves various water based products from microbial spoilage.
  • a single active compound cannot provide an effective overall control of microorganisms due to efficacy gaps against certain microorganism types or the requirement of high use concentrations which prevent the chemistry from becoming a commercially viable product due to cost to treat barriers.
  • U.S. Pat. App. Pub. No. 2007/0078118 discloses synergistic combinations of N-methyl-1,2-benzisothiazolin-3-one (MBIT) with other biocides.
  • MBIT N-methyl-1,2-benzisothiazolin-3-one
  • MBIT is an ingredient often used in the home and personal care market it would be advantageous to be able to minimize the amount of MBIT used and combine it with a natural ingredient, while maintaining the same or better effectiveness.
  • the problem addressed by this invention is to provide such additional combinations of microbicides.
  • Combinations of different antimicrobial compounds or other ingredients in the formulation especially if they are synergistic, can broaden activity against various microorganisms, lessen overall biocide usage, aid in the minimization of environmental footprint and also expand potential market applications.
  • This invention addresses the potential problems mentioned above and provides insight to MBIT synergistic activity with combinations of several natural ingredients used in cosmetic skin care applications or house hold products that are known to have specific function such as topical therapeutic effect, antioxidant, skin conditioning, etc. and may or may not have antimicrobial activities.
  • the present invention is directed to a microbicidal composition
  • a microbicidal composition comprising: (a) N-methyl-1,2-benzisothiazolin-3-one; and (b) at least one natural organic acid.
  • the invention is also directed to a method of inhibiting the growth of or controlling the growth of microorganisms comprising the step of adding the microbicidal composition to a household products; cosmetics; toiletries; shampoos; soaps; detergents; industrial cleaners; floor polishes; laundry rinse water; leather and leather products; textiles; textile products; agriculture adjuvant preservation; surfactant preservation; medical devices; diagnostic reagent preservation; toilet bowls; recreational water; pools; and spas.
  • a coating composition comprising: (a) N-methyl-1,2-benzisothiazolin-3-one; and (b) at least one natural organic acid wherein the weight ratio of N-methyl-1,2-benzisothiazolin-3-one to natural organic acid may be from 1:10 to 1:33,333.
  • MBIT is N-methyl-1,2-benzisothiazolin-3-one.
  • natural organic acid synonymous with “organic acid” refers to azelaic acid (CAS No. 123-99-9), lactic acid (CAS No. 50-21-5), ferulic acid (CAS No. 1135-24-6), and undecylenic acid (CAS No. 112-38-9), preferably azelaic acid (CAS No. 123-99-9), lactic acid (CAS No. 50-21-5), and undecylenic acid (CAS No. 112-38-9).
  • microbicide synonymous with “antimicrobial” refers to a compound capable of killing, inhibiting the growth of or controlling the growth of microorganisms at a locus; microbicides include bactericides, fungicides and algaecides.
  • microorganism includes, for example, fungi (such as yeast and mold), bacteria, and algae, preferably fungi and bacteria.
  • locus refers to an industrial system or product subject to contamination by microorganisms.
  • compositions of the present invention unexpectedly have been found to provide enhanced microbicidal efficacy at a combined active ingredient level lower than that of the individual microbicides. Additional microbicides beyond those listed in the claims may be present in the composition.
  • the antimicrobial composition comprises N-methyl-1,2-benzisothiazolin-3-one and an organic acid.
  • the antimicrobial composition comprises N-methyl-1,2-benzisothiazolin-3-one and azelaic acid.
  • a weight ratio of N-methyl-1,2-benzisothiazolin-3-one to azelaic acid is from 1:50 to 1:105.
  • the antimicrobial composition comprises N-methyl-1,2-benzisothiazolin-3-one and lactic acid.
  • a weight ratio of N-methyl-1,2-benzisothiazolin-3-one to lactic acid is from 1:125 to 1:33,333.
  • the antimicrobial composition comprises N-methyl-1,2-benzisothiazolin-3-one and undecylenic acid.
  • a weight ratio of N-methyl-1,2-benzisothiazolin-3-one to undecylenic acid is from 1:10 to 1:212.
  • the microbicides in the composition of this invention may be used “as is” or may first be formulated with a solvent or a solid carrier.
  • suitable solvents include, for example, water; glycols, such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, polyethylene glycol, and polypropylene glycol; glycerin, glycol ethers, such as propylene glycol ether, diethyleneglycol monobutyl ether, dipropymyne glycol methyl ether, ethylene glycol ethylether, ethylene glycol monobutyl ether; alcohols, such as methanol, ethanol, propanol, isopropanol, phenethyl alcohol, phenoxyethanol and phenoxypropanol; ketones, such as acetone and methyl ethyl ketone; esters, such as ethyl acetate, butyl acetate, triacetyl citrate, and
  • the solvent is selected from water, glycols, glycol ethers, esters and mixtures thereof.
  • suitable solid carriers include, for example, cyclodextrin, silicas, clay, animal fat, diatomaceous earth, waxes, cellulosic materials, alkali and alkaline earth (e.g., sodium, magnesium, potassium) metal salts (e.g., chloride, nitrate, bromide, sulfate) and charcoal.
  • the formulation may optionally contain surfactants.
  • surfactants they are generally in the form of emulsifiable concentrates, emulsions, microemulsive concentrates, or microemulsions.
  • Emulsifliable concentrates form emulsions upon the addition of a sufficient amount of water.
  • Microemulsive concentrates form microemulsions upon the addition of a sufficient amount of water.
  • Such emulsive and microemulsive concentrates are generally well known in the art; it is preferred that such formulations are free of surfactants.
  • U.S. Pat. No. 5,444,078 may be consulted for further general and specific details on the preparation of various microemulsions and microemulsive concentrates.
  • a microbicide component also can be formulated in the form of a dispersion.
  • the solvent component of the dispersion can be an organic solvent or water, preferably water.
  • Such dispersions can contain adjuvants, for example, co-solvents, chelants or sequestrans thickeners, anti-freeze agents, dispersants, fillers, pigments, surfactants, biodispersants, sulfosuccinates, terpenes, furanones, polycations, stabilizers, scale inhibitors and anti-corrosion additives.
  • microbicide components of the present invention may be added to a locus sequentially, simultaneously, or may be combined before being added to the locus. It is preferred that the first microbicide and the second microbicide component be added to a locus simultaneously or sequentially.
  • each individual component may contain adjuvants, such as, for example, solvent, thickeners, anti-freeze agents, colorants, sequestrants (such as ethylenediamine-tetraacetic acid, ethylenediaminedisuccinic acid, iminodisuccinic acid and salts thereof), dispersants, surfactants, biodispersants, sulfosuccinates, terpenes, furanones, polycations, stabilizers, scale inhibitors and anti-corrosion additives.
  • adjuvants such as, for example, solvent, thickeners, anti-freeze agents, colorants, sequestrants (such as ethylenediamine-tetraacetic acid, ethylenediaminedisuccinic acid, iminodisuccinic acid and salts thereof), dispersants, surfactants, biodispersants, sulfosuccinates, terpenes, furanones, polycations, stabilizers, scale inhibitors and anti-corrosion additive
  • microbicidal compositions of the present invention can be used to inhibit the growth of microorganisms) by introducing a microbicidally effective amount of the compositions onto, into, or at a locus subject to microbial attack.
  • Suitable loci include, for example: industrial process water; electrocoat deposition systems; cooling towers; air washers; gas scrubbers; mineral slurries; wastewater treatment; ornamental fountains; reverse osmosis filtration; ultrafiltration; ballast water; evaporative condensers; heat exchangers; pulp and paper processing fluids and additives; starch; plastics; emulsions; dispersions; paints; latices; coatings, such as varnishes; construction products, such as mastics, caulks, and sealants; construction adhesives, such as ceramic adhesives, carpet backing adhesives, and laminating adhesives; industrial or consumer adhesives; photographic chemicals; printing fluids; household products, such as bathroom and kitchen cleaners and sanitary wipes; cosmetics; toiletries
  • microbicidal compositions of the present invention are used to inhibit the growth of microorganisms at a locus selected from household products; cosmetics; toiletries; shampoos; soaps; detergents; industrial cleaners; floor polishes; laundry rinse water; leather and leather products; textiles; textile products; agriculture adjuvant preservation; surfactant preservation; medical devices; diagnostic reagent preservation; toilet bowls; recreational water; pools; and spas.
  • the specific amount of the composition of this invention necessary to inhibit or control the growth of microorganisms and higher aquatic life forms in a locus depends upon the particular locus to be protected. Typically, the amount of the composition of the present invention to control the growth of microorganisms in a locus is sufficient if it provides from 0.1 to 1,000 ppm of the isothiazoline ingredient of the composition in the locus. It is preferred that the isothiazolone ingredients of the composition be present in the locus in an amount of at least 0.5 ppm, more preferably at least 4 ppm and most preferably at least 10 ppm. It is preferred that the isothiazolone ingredients of the composition be present in the locus in an amount of no more than 1000 ppm, more preferably no more than 500 ppm, and most preferably no more than 200 ppm.
  • the microbicidal compositions of the present invention may be included in a coating composition.
  • N-methyl-1,2-benzisothiazolin-3-one and the at least one organic acid may be added to the coating composition separately or as a mixture or any combination thereof.
  • Preferred coating compositions are liquid.
  • Coating compositions may be aqueous or non-aqueous.
  • Aqueous coating compositions generally contain 30% or more water by weight of the mixture, based on the weight of the coating composition.
  • the antimicrobial compositions are used to inhibit growth of algae, bacteria, and/or fungi, preferably bacteria, and/or fungi. It is contemplated that some embodiments may contain one or more additional antimicrobial compound.
  • the minimum inhibitory concentration (MIC) of a microbicide is the lowest concentration tested under a specific set of conditions that prevents the growth of added microorganisms.
  • the microorganisms tested were Escherichia coli ( E. coli , ATCC #8739), a yeast, Candida albicans ( C. albicans , ATCC #10231) and mold, Aspergillus niger ( A. niger , ATCC #16404).
  • MBIT synergy with a secondary biocide was determined by evaluating the minimum biocide or biocide blend concentration required to inhibit microbial growth. All studies were conducted using a 96 well microtiter plate format. For all studies, 200 ⁇ l of microbial growth media, containing various concentrations of MBIT alone, the secondary biocide alone, or combinations of both biocide chemistries, was added to individual wells of a microtiter plate. Specifically, Tryptic Soy Broth (TSB) was utilized for bacteria ( E.
  • TTB Tryptic Soy Broth
  • coli ATCC #8739
  • YMB Yeast Malt Extract Broth
  • PDB Potato Dextrose Broth
  • Test organisms at a final concentration of 10 4 CFU/mL or 10 4 spores/mL, were applied to each well in parallel experiments to initiate the MIC evaluations.
  • Growth medium containing no biocide was utilized as a control in each experimental setup to confirm the growth viability of each organism. Eight concentrations (2-fold dilutions) of each individual biocide were evaluated in the microbial growth inhibition studies in addition to the 64 possible combinations of these biocide concentrations.
  • microorganisms are representative of natural contaminants in many consumer and industrial applications.
  • the plates were visually evaluated for microbial growth (turbidity) to determine the MIC after various incubation times at 25° C. (yeast and mold) or 30° C. (bacteria).

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Emergency Medicine (AREA)
  • Biochemistry (AREA)
  • Textile Engineering (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Detergent Compositions (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)
US15/108,485 2013-12-30 2014-12-10 Microbicidal composition Active US9642367B2 (en)

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US201361921612P 2013-12-30 2013-12-30
PCT/US2014/069523 WO2015102833A1 (en) 2013-12-30 2014-12-10 Microbicidal composition
US15/108,485 US9642367B2 (en) 2013-12-30 2014-12-10 Microbicidal composition

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JP7352719B2 (ja) * 2020-02-27 2023-09-28 日本曹達株式会社 殺菌剤組成物

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US20090023688A1 (en) 2007-07-18 2009-01-22 Richard Levy Microbicidal composition
US20090163445A1 (en) 2007-12-20 2009-06-25 Diehl Megan A Synergistic microbicidal compositions
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US20090023688A1 (en) 2007-07-18 2009-01-22 Richard Levy Microbicidal composition
US20090163445A1 (en) 2007-12-20 2009-06-25 Diehl Megan A Synergistic microbicidal compositions
EP2570502A1 (de) 2011-09-13 2013-03-20 LANXESS Deutschland GmbH Flüssige Wirkstoffpräparationen zum fungiziden Schutz von collagenfaserhaltigen Substraten

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